Planning your perfect Tuscany itinerary

Picture yourself wandering through picturesque vineyard landscapes, sipping world-class wines, savoring delectable cuisine, and immersing yourself in centuries-old culture. Welcome to Tuscany, where every corner of this Italian gem tells a story waiting to be discovered. Here is our guide to creating the perfect Tuscany itinerary.

Why Visit Tuscany?

Tuscany beckons with its unique tapestry of history, nature, and culinary wonders. 

From the enchanting allure of charming hilltop villages to the artistic marvels of Renaissance Florence, you’ll find Tuscany is a well-known travel destination for a reason. Many visit this region to embark on a wine-tasting odyssey through vineyards that have birthed renowned elixirs like Barolo and Barbaresco. 

Any Tuscany itinerary is sure to offer an intoxicating blend of cultural richness, natural beauty, and exquisite flavors.

Best places to see in Tuscany

In Tuscany, every town and city unveils a treasure trove of experiences. Whether you're exploring the world-renowned architectural wonders of Florence or wandering through the cobbled lanes of San Gimignano, you’ll find magic in every corner of Tuscany.

Florence

The capital of Tuscany, Florence is a city of artistic and architectural masterpieces. Don't miss the Florence Cathedral, Uffizi Gallery, Accademia Gallery (home to Michelangelo's David), and the iconic Ponte Vecchio bridge.

San Gimignano

Often referred to as the "Medieval Manhattan" due to its numerous towers, San Gimignano is a remarkably well-preserved medieval town. Wander its cobblestone streets, savor delectable gelato, and revel in panoramic vistas from its towers.

Pienza

Recognized as a UNESCO World Heritage site, Pienza is celebrated for its Renaissance architecture and urban layout. Explore Piazza Pio II, visit the cathedral, and indulge in the local specialty—pecorino cheese.

Chianti Region

A haven for wine enthusiasts, the Chianti region is renowned for its vineyards and wineries. Embark on a wine tour to savor world-class Chianti Classico wines while soaking in the picturesque countryside.

Consider taking your time to explore the Chianti region at a more leisurely pace to fully appreciate its beauty and charm.ambianc

Lucca

The walled city of Lucca is famous for its Renaissance fortifications and enchanting ambience. Stroll or cycle atop the walls for stunning views, discover the historic center, and dine in authentic trattorias.

Want to explore Europe even more? We have prepared the most convenient European itineraries for you to explore the continent.

How to get to Tuscany

Embarking on your Tuscan adventure is a seamless affair, with multiple pathways leading to this alluring region.

By Air

Fly into Florence or Pisa, both well-connected to major European cities. Florence Airport provides easy access to the heart of Tuscany, while Pisa Airport offers a gateway to the western coast.

By Train

Italy's efficient rail network connects Tuscany to major cities like Rome and Milan. Arriving by train allows you to enjoy scenic views along the way.

By Road: Rental Car

If you prefer the freedom of the open road, Tuscany is accessible by car. The well-maintained highway network ensures a smooth journey, with opportunities to explore charming towns en route.

7-day Tuscany itinerary

Explore the enchanting heart of Tuscany with our meticulously designed Tuscany wine & food itinerary created by our local travel experts.  In just one week, delve into the heart of this iconic Italian region, celebrated for its vibrant culture and awe-inspiring scenery.

Itinerary overview

You’ll begin this 7-day Tuscany itinerary in Florence with a tour of the Oltrarno district and the next day you will be transferred to the hotel in San Gimignano.

Take a scenic hike, visit an olive oil mill, and enjoy a boutique winery tour with a traditional Tuscan lunch. Discover wine-making secrets during a Vertical Wine Tasting. Read more.

Explore Montepulciano's vineyards, savor regional foods, and conclude with a Chianti Food and Wine Pairing. Depart from Florence Airport on day seven.

Want to skip the hassle of planning? Have us create your trip for you.

Day 1

• Arrival in Florence
• Immerse yourself in the local culture with a guided tour of the Oltrarno district, visiting the workshops of skilled artisans

Day 2

• Transfer to San Gimignano
• Take this day to explore the surrounding area at your own leisure

Day 3

• Morning hike through the Tuscan countryside
• Visit an olive oil mill, followed by a guided exploration of a boutique winery.
• Traditional Tuscan lunch

Day 4

• Lunch at a Tuscan vineyard
• Dive into a Vertical wine-tasting experience featuring 15 distinct Tuscan wine products
• Delve into the art of winemaking with an educational lesson

Day 5

• Wine Tour in Montepulciano
• Explanation of winery history and philosophy, as well as fermentation and aging process insights
• Explore the vineyards
• Winetasting with regional foods

Day 6

• Chianti Food and Wine Pairing
• Venture into the depths of the cellars for a tasting of wines and regional products
• Balsamic vinegar tasting

Day 7

• Departure from Tuscany
• Transfer to Florence Airport

Create your Tuscany itinerary with us

Reach out to our Italy local travel experts when you're ready to embark on your Italian adventure, and we'll tailor a wonderful journey exclusively for you. Collaborate with us to perfect your personalized itinerary, ensuring it aligns with your every desire. Don't hesitate to browse our ready-made Italy itineraries for inspiration, knowing that each can be adjusted to suit your individual tastes.